The present invention provides novel 2-methoxyimino-2-(pyridinyloxymethyl)phenyl acetamide compounds with polyether substituents on the pyridine ring, their use as fungicidal compounds, and their use in fungicidal compositions comprising at least one of the 2-methoxyimino-2-(pyridinyloxymethyl)phenyl acetamide compounds as the active ingredient.
This invention provides novel 2-methoxyimino-2-(pyridinyloxymethyl)phenyl acetamide compounds of formula (1), below 
wherein
m is an integer 0-3;
L is xe2x80x94Oxe2x80x94, xe2x80x94CH2xe2x80x94, xe2x80x94SOnxe2x80x94, -CH2Oxe2x80x94, xe2x80x94OCH2xe2x80x94, xe2x80x94CH2Sxe2x80x94, xe2x80x94SCH2xe2x80x94, xe2x80x94CHxe2x95x90CHxe2x80x94, xe2x80x94Cxe2x89xa1Cxe2x80x94, or 
wherein n is an integer 0-2;
X, Y, and Z are each independently H, C1-6 alkyl, C1-6 alkoxy, halo-C1-6 alkyl, halo-C1-6 alkoxy, halo, nitro, carbo-C1-6 alkoxy, cyano, C1-6 alkylthio, or halo-C1-6 alkylthio;
W is H, halogen, C1-4 alkyl, C1-4 alkoxy, halo-C1-4 alkyl, or C1-4 alkylthio;
A is O, S, NR3, OCH2, SCH2;
B is O or S;
R1 is a C1-C4 alkyl group (optionally substituted by alkenyl, cycloalkyl, alkoxy, alkoxycarbonyl, arylalkyl, cyano, cyanoalkyl, halo, or haloalkyl), optionally substituted phenyl, or an optionally substituted aryl or heteroaryl ring;
R2 is a C1-C8 alkyl, (optionally substituted by alkenyl, cycloalkyl, alkoxy, alkoxycarbonyl, arylalkyl, cyano, cyanoalkyl, halo, or haloalkyl), optionally substituted phenyl, or an optionally substituted aryl or heteroaryl ring;
or the group R1xe2x80x94Bxe2x80x94R2 can be an optionally substituted 4-6 membered saturated or unsaturated heterocyclic ring;
or the group xe2x80x94Axe2x80x94R1xe2x80x94Bxe2x80x94R2 can be an optionally substituted 4-6 membered saturated or unsaturated heterocyclic ring containing 2 or more heteroatoms; and
R3 is H or C1-6 alkyl.
The present invention also provides compositions comprising one or more compounds of Formula (1) in combination with phytologically-acceptable carriers and/or diluents. Methods for the use of compounds of formula (1) and compositions comprising one or more compounds of formula (1) are also provided.
Throughout this document, all temperatures are given in degrees Celsius and all percentages are weight percentages, unless otherwise stated.
The term xe2x80x9chalogenxe2x80x9d or xe2x80x9chaloxe2x80x9d refers to F, Cl, I, or Br.
The term xe2x80x9calkylxe2x80x9d, xe2x80x9calkenylxe2x80x9d, or xe2x80x9calkynylxe2x80x9d refers to a straight chain or branched chain carbon radical containing the designated number of carbon atoms.
The term xe2x80x9calkoxyxe2x80x9d refers to a straight or branched chain alkoxy group.
The term xe2x80x9chalo alkylxe2x80x9d refers to a straight or branched alkyl group substituted with one or more halo atoms. The term xe2x80x9chalo alkoxyxe2x80x9d refers to an alkoxy group substituted with one or more halo atoms.
The term xe2x80x9carylxe2x80x9d or xe2x80x9cPhxe2x80x9d refers to a phenyl group. The term xe2x80x9csubstituted arylxe2x80x9d refers to a phenyl group substituted with C1-C6 alkyl, C1-C6 alkoxy, halo-C1-C6 alkyl, halo-C1-C6 alkoxy, halo, nitro, carbo-C1-C6 alkoxy, or cyano. The term xe2x80x9cheteroarylxe2x80x9d refers to pyridyl, pyridinyl, pyrazinyl, pyridazinyl or thiophene.
The term xe2x80x9cMexe2x80x9d refers to a methyl group. The term xe2x80x9cEtxe2x80x9d refers to an ethyl group. The term xe2x80x9cPrxe2x80x9d refers to a propyl group. The term xe2x80x9cBuxe2x80x9d refers to a butyl group. The term xe2x80x9cEtOAcxe2x80x9d refers to ethyl acetate.
The term xe2x80x9cppmxe2x80x9d refers to parts per million. The term xe2x80x9cpsixe2x80x9d refers to pounds per square inch.
The term xe2x80x9cM.P.xe2x80x9d refers to melting point. The term xe2x80x9cbpxe2x80x9d refers to boiling point.
While all the compounds of this invention have fungicidal activity, certain classes of compounds may be preferred for reasons such as, for example, greater efficacy or ease of synthesis.
A preferred class includes those compounds of Formula (2), below 
wherein the substituents are as defined in Formula (1), above.
A more preferred class includes those compounds of Formula (3), below 
wherein L is either xe2x80x94Oxe2x80x94, xe2x80x94CH2Oxe2x80x94, or xe2x80x94OCH2xe2x80x94, and the other substituents are as defined in Formula (1), above.
A next more preferred class includes those compounds of Formula (4), below 
wherein the substituents are as defined in Formula (1), above.
A next more preferred class includes those compounds of Formula (5), below 
wherein the substituents are as defined in Formula (1), above.
A next more preferred class includes those compounds of Formula (5-1), below 
wherein the substituents are as defined in Formula (1), above.